14. Synthetic Techniques
Alkynide Alkylation
14. Synthetic Techniques
Alkynide Alkylation - Video Tutorials & Practice Problems
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Get a 10 bullets summary of the topicOrganometals aren't the only way to create new carbon-carbon bonds. It turns out we can use a sodium alkynide (nucleophile) as well to react with alkyl halides and other electrophiles to form a new C-C bond as well.
1
concept
Sodium Alkynide Alkylation
Video duration:
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Once we create these triple bond nucleophiles and use them in our synthesis, we will will also learn how to get rid of them and transform them to double bonds (cis and trans) and single bonds.
Let's get to work. These will be multi-step transformations. Do your best to see if you can fill in the correct reagents!
2
Problem
ProblemPropose a synthesis:
A
1) H2/Lindlar's Catalyst
2) KMnO4, OH-, Δ / H+ 3) NaBH4
4) CH3MgBr
2) KMnO4, OH-, Δ / H+ 3) NaBH4
4) CH3MgBr
B
1) LiAlH
2) CH3Cl 3) H2/Pt
2) CH3Cl 3) H2/Pt
C
1) NaNH2
2) CH3Br 3) H2/Lindlar's catalyst
2) CH3Br 3) H2/Lindlar's catalyst
D
1) O3, Me2S
2) EtLi / H3O+ 3) LDA
2) EtLi / H3O+ 3) LDA
3
Problem
ProblemPropose a synthesis:
A
1) Cl2
2) CH3ONa (excess) 3) CH3Br
4) H2/Pt
2) CH3ONa (excess) 3) CH3Br
4) H2/Pt
B
1) O3, Me2S
2) EtLi / H3O+ 3) LDA
2) EtLi / H3O+ 3) LDA
C
1) Br2
2) NaNH2 (2 eq.) 3) H3O+/H2O
4) CH3MgBr / H3O+
2) NaNH2 (2 eq.) 3) H3O+/H2O
4) CH3MgBr / H3O+
D
1) Br2
2) NaNH2 (excess) 3) CH3I
4) Na/Liq. NH3
2) NaNH2 (excess) 3) CH3I
4) Na/Liq. NH3
4
Problem
ProblemA
1) Br2 / Δ
2) LDA 3) Br2
4) NaNH2 (2 eq.) 5) H3O+/H2O
6) EtMgBr / H3O+
2) LDA 3) Br2
4) NaNH2 (2 eq.) 5) H3O+/H2O
6) EtMgBr / H3O+
B
1) Br2 / Δ
2) LiTMP 3) Br2
4) NaNH2 (2 eq.) 5) O3, Me2S
6) CH3CH2CH2MgBr
2) LiTMP 3) Br2
4) NaNH2 (2 eq.) 5) O3, Me2S
6) CH3CH2CH2MgBr
C
1) Br2 / Δ
2) KOC(CH3)3 3) Br2
4) NaNH2 (excess) 5) CH3CH2I
6) H2/Pt
2) KOC(CH3)3 3) Br2
4) NaNH2 (excess) 5) CH3CH2I
6) H2/Pt
D
1) Cl2 / Δ
2) NaH 3) Br2
4) NaNH2 (2 eq.) 5) KMnO4, OH-, Δ / H+ 6) CH3CH2CH2MgBr
2) NaH 3) Br2
4) NaNH2 (2 eq.) 5) KMnO4, OH-, Δ / H+ 6) CH3CH2CH2MgBr
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PRACTICE PROBLEMS AND ACTIVITIES (29)
- Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.(f) &...
- Show how you would accomplish the following synthetic conversions. You may use any additional reagents and sol...
- a. Show how the following compounds can be prepared, using ethyne as one of the starting materials:2. 1-phenyl...
- Show how you would synthesize the following compounds, starting with acetylene and any compounds containing ...
- How can the following compounds be prepared using ethyne as the starting material?c. <IMAGE>
- Show how each of the following compounds can be synthesized from the given starting materials:b. <IMAGE>
- (••) Suggest a method for synthesizing the following alkynes using an alkyne and an alkyl halide. [There are t...
- When doing synthesis, you will often find yourself repeating the same series of steps. To see this in action, ...
- Show how each of the following compounds can be prepared using the given starting material, any needed inorgan...
- Show how each of the following compounds can be synthesized from the given starting materials:d. <IMAGE>
- Predict the products formed when <IMAGE> reacts with the following compounds.(d) cyclohexanone(e) CH3CH2...
- The application box in the margin of page 437 states, “The addition of an acetylide ion to a carbonyl group is...
- a. Show how the following compounds can be prepared, using ethyne as one of the starting materials: 1. 1-pent...
- How could the following compounds be synthesized from acetylene? b.
- Reaction of the acetylide with the epoxide shown will not form the desired product. What side reaction occurs ...
- Beginning with the molecules on the left of each chemical equation, synthesize the molecules shown. While ther...
- (•••) Beginning with the molecules on the left, provide a synthesis of the molecule on the right. The ideal nu...
- (•••) Synthesize the following molecules beginning with only organic molecules containing three carbons or few...
- (•••) Synthesize the following molecules beginning with only organic molecules containing three carbons or few...
- For each of the following target molecules, design a multistep synthesis to show how it can be prepared from t...
- Show how each of the following compounds can be synthesized from the given starting materials: c.
- Show how each of the following compounds can be prepared using the given starting material, any needed inorgan...
- Show how each of the following compounds can be prepared using the given starting material, any needed inorgan...
- Show how the following compound can be prepared from the given starting material. Draw the structure of the co...
- Show how you would synthesize each compound, beginning with acetylene and any necessary additional reagents a....
- Show how you would synthesize each compound, beginning with acetylene and any necessary additional reagents b....
- Show how you would synthesize 2-phenylhex-3-yn-2-ol, starting with acetophenone (PhCOCH3) and any other reagen...
- (••) Complete the following synthesis by providing the necessary reagents.<IMAGE>
- Beginning with the molecules on the left of each chemical equation, synthesize the molecules shown. While ther...